Organic Nomenclature http://openchemistry.in/

MASTERING ORGANIC CHEMISTRY •

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1

The IUPAC Systematic Approach to Nomenclature Identify Root:-Find the parent hydrocarbon. This is based on the longest continuous carbon chain. If there are chains of equivalent length, then select the one with the most branch points as the parent.

•

Number the chain:-Number the atoms in the parent chain, beginning at the end nearer the first branch point. If there is branching an equal distance from both ends, then consider the next branch point. • Identify the substituents:- Identify and number the substituents. Remember there must be as many numbers as there as substitutents. • Writing the name:- Write out the name as a single word, using hyphens to separate the different prefixes and commas to separate the numbers. If two or more different substitutents are present, cite them in alphabetical order. With identical substituents, use the prefix di-, tri-, tetra- etc. as required. Ignore these prefixes when alphabetising. • If a substituent has subranching (ie. its complex) then reapply the first 4 steps as if it were a compound. Numbering must begin at the point of attachment. Now set this substituent in parentheses. Naming the parent chain: Here is a list of the root names for the hydrocarbon chains C1 = meth- C2 = ethoctC9 = non-

C3 = propC10 = dec-

C4 = butC5 = pentC6 = hex- C7 = hept- C8 = C11 = undec- C12 = dodec- C18 = octadec- C20 = icos-

IUPAC Rules for Naming Organic Molecules To name a compound using the IUPAC system, follow the steps shown (if applicable) in the following order. Step 1 Determine the principle functional group in the compound. When a compound contains more than one group in Table 1, the principle group is that which has the highest precedence. This group will be cited as a suffix; all other groups are cited as prefixes. Functional Group -(C)aOOH -COOH -SO2OH -C(O)OC(O)-(C)OOR -COOR -(C)OX -COX -(C)ONH2 -CONH2 -(C)≡N -C≡N -(C)HO -CHO >(C)=O -OH -SH -NH2 >NH >C=C< -C≡C-X, -R, -OR -Ar, -NO2 -NO, -N3 =N2, -SR a

Suffix if Highest Precedence -oic acid -carboxylic acid -sulfonic acid -oic anhydride alkyl -oate alkyl carboxylate -oyl halide -carbonyl halide -amide -carboxamide -nitrile -carbonitrile -al -carbaldehyde -one -ol -thiol -azane (-amine) -azane (-imine) -ene -yne -

Prefix if Lower Prededence carboxysulfoalkoxy-oxohalo-oxohalocarbonylamino-oxoaminocarbonylcyanooxoformyloxohydroxysulfanylazanyl- (-amino) azanylidene* ** halo-, alky-l, alkoxyaryl-, nitronitroso-, azidodiazo-, (R)-sulfanyl-

(C) designates a carbon atom included in the parent hydrocarbon (part of the longest chain or ring.

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* and ** These are always used as a suffix. If a higher priority group is present in the molecule the suffix is changed to –en– or –yn– and is followed by the suffix of the higher priority group. Step 2 Determine the parent hydrocarbon (principle chain or ring system system): (a) If the principle group occurs in a chain, the principle chain is selected as (i) the chain containing the functional group of the highest seniority as the parent. OH

2-(propan-1-yl)pentan-1-ol (ii) If more than one such choice is possible, select the chain with the maximum number of multiple bonds. 2-(hexan-1-yl)buta-1,3-diene (iii) If (i) and (ii) together are not definitive, then choose the longest chain. (iv) If two chains of the same length are possible, choose the one with the maximum number of substituent groups. O

H

2-(butan-1-yl)-4-methylhexanal The parent chain here contains six carbon atoms. If the principle functional group occurs in a cyclic system, that cyclic system forms the parent.

(b)

OH

2-(octan-1-yl)cyclohexanol

2-(hexan-1-yl)cyclopentene

Step 3 Name the parent structure of and the principle group(s). Give the parent name the same name as if it were an alkane, but replace –ane with the suffix characteristic of the functional group of the highest priority (Table 1). Note: Multiple unsaturation in hydrocarbons is indicated by the numerical prefixes di-, tri-, etc. In such cases, however, the ending –ane of the parent alkane is replaced with –adiene, –atriene, etc. leaving the “a” in the root alkane name whenever the first letter of the suffix is a consonant to make the name easier to pronounce. Thus we get alkadienes, alkatrienes, alkadiynes, etc. Step 4 Complete the number system. (a) Number the carbon atoms consecutively from the end of the chain nearer the functional group of the highest priority. 1 2

3

5

4,5-dimethylhexan-3-one

6

4 O

(b) 1

If the same number for the functional group of highest priority is obtained in both directions, the correct IUPAC name is the one that contains the lowest substituent numbers.

2

(c) (d)

6

4

2,4-dimethylhex-3-ene

5

3

The substituent numbers are 2 and 4. If we numbered from the other end, the substituent numbers would have been 3 and 5. 2+4 is a lower numbering system than 3+5. If the first substituents occur at an equal didtance from each end of the chain, number the end nearer a second substituent. If still the same, continue until the first point of difference. If numbering for either end gives the same set of numbers, number from the end with the substituent that comes first in alphabetical order. 6 2 5 4

1

2-chloro-5-methylhex-3-ene

3 Cl

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In monosubstituted cycloalkanes and benzene derivatives. The carbon to which the substituent is bonded is always number 1. If there is only one substituent, the locant number “1” is omitted. However, the number one is required in polysubstituted compounds. NO 2

CH3

OH I

Cl

(f)

Br

Cyclopentanol 1-chloro-2-methylcyclohexane 2-bromo-4-iodo-1-nitrobenzene In polysubstituted cyclic compounds, the starting point and the direction of numbering are chosen to give the lowest numbering system. The starting point is chosen according to the following factors: (i) The principle functional group named as the suffix is always given the lowest possible number. Because certain cyclic systems have fixed numbering systems, it is not always possible to place a substituent on carbon number 1. 6 HO

4

NO 2 1

5

2

4

1

8

CH3

5

Br

3

OH 7

2

6

3

2

6 N 1

3

5 4 IUPAC: 3-nitrobenzen-1-ol 3-methylazabenzene 7-bromonaphthalene-2-ol (3-nitrophenol accepted) (3-methylpyridine accepted ) (7-bromo-2-naphthol accepted) Note: When one heteroatom is present in the ring the number 1 is assigned to that atom. If more than one is present then we use the number 1 on the O, S, or N in that order of priority. 4 3 4 3 4 N3

5 N

2

S 2 O O 1 1 IUPAC: oxole(Furan accepted) 1,2-oxathiolane (ii) Lowest numbering for multiple bonds in cyclic compounds. 5

5

4

6

2 N 1

1,3,5-triazine

2

Cl

OH

CH3 5

3

3

1

6

2

4

6

1

CH3

5

5-chloro-3-methylcyclohexene 6-methylcyclohex-3-en-1-ol Note: In naming cycloalkenes, the double bond is located between C1 and C2, and the “1” is usually omitted in the name. The ring is numbered clockwise or counterclockwise to give the first substituent the lower number. However, when functional group with a higher priority than an alkene is present, the carbon bonded to the higher priority group becomes C1 and then multiple bonds are considered for lowest possible numbering. (iii) Lowest numbering for first substituent (or first point of difference). Cl

CH3

3 2 4 5 6 1

OH

CH2CH2CH3

5 6 1 4 2 3 Cl

CH3

4-chloro-2-methylcyclohexan-1-ol 4-chloro-2-methyl-1-(propan-1-yl)cyclohexane (iv) If the same numbers will result from numbering in either direction, give the lowest number for the substituent that is cited first in the name. 4

Br

CH3 3 2 1

4 5

CH2CH3

Cl

3 6

2 1 O

2-ethyl-3-methylnaphthalene 3-bromo-5-chlorocyclohexanone Step 5 Name alkyl groups, halides, and other substituents and determine their position on the chain by the numbering system established by step 4. Step 6 Assign the stereochemistry to chiral carbon atoms (stereocenters) and the double bond(s): B-7. JAWAHAR NAGAR.Main Road ,Kota.

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Disubstituted alkenes may be named in two ways: (i) using terms cis- and trans- or (ii) using terms (E) or (Z). Note: Use of (E) and (Z) stereocenters is preferred. However, the cis-trans terms are accepted.

(E)-pent-2-ene or trans-pent-2-ene (Z)-hex-3-ene or cis-hex-3-ene (b) Triand tetrasubstituted alkenes may only be named using the (E-Z) system. 6 1 5

(E)-2,3,5-trimethylhex-3-ene

3

2

4

(c)

Disubstituted cycloalkanes may be named using the terms cis-trans or (R-S). CH3

cis-1-chloro-4-methylcyclohexane (R-S) system not applicable here

Cl

CH3

H

trans-3-methylcyclopentanol (1R,3R)-3-methylcyclopentanol Chiral carbon atoms are assigned (R) or (S) configuration. H

HO

(d)

(S)-5-methylhexan-3-ol H HO

OH H COO

(2S,3R)-2-amino-3-hydroxybutanoic acid common name: threonine

H

H3N

(e) When both (R-S) and (E-Z) stereodescriptors are present, they are placed in parentheses followed by a hyphen; each stereodescriptor is immediately preceded by its associated number and they are arranged in numerical order. H OH Cl

CH3

(3S,4E)-6-methylhept-4-en-3-ol (2Z,4E,6R)-6-chloro-6-methylocta-2,4-diene Step 7 Compounds with multiple bonds and triple bonds have the following suffixes: –adiene, – adiyne, –atriene, –atetraene, and so on. Specify the location of each multiple bond by a locant number placed between the “a” and diene, diyne, triene, etc. (E)-2-ethylhexa-1,4-diene previously: (E)-2-ethyl-1,4-hexadiene Step 8 Compounds with both double and triple bonds are called enynes. Start the numbering of enynes from the end nearest the first multiple bond, regardless of type. When a double bond is the same distance 8 number. from one end as a triple bond from the other end, assign the double bond the lower 7 6

2

4

1

2

3

5

7

1

3

6

4 5

(E)-hept-5-en-1-yne (E)-oct-2-en-6-yne Step 9 Write the complete name of the compound as a single word with the correct locant numbers for all substituents, which are listed in alphabetical order. The prefixes di, tri, tetra, etc. do not alter the alphabetical ordering of the substituents. The stereochemistry is indicated by placing the appropriate prefix within parentheses followed by a hyphen in front of the name. Cl 1 6

2 5 4

(E)-5-chloro-3-methyl-3-en-2-one

3 O

O

4-ethyl-2,5-dimethylhexanal (a)

The numbers indicating locations of substituents are separated by commas.

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The letters and numbers are joined by hyphens. When naming esters, no hyphen is placed between the name of the alkyl group derived from the alcohol and the name of the acid from which the ester was derived. O methyl butanoate O

Step 10 A complex substituent is named by applying the above steps just as if the substituent were a compound itself. We begin numbering the sidechain at the point of attachment to the parent hydrocarbon giving the carbon at the point of attachment the locant of C1. We then give this substituent the suffix –yl. We put this name in parentheses and in front of the parentheses we place the locant number on the parent hydrocarbon. SH

OH Br

2-(bromomethyl)benzenethiol

4

1

OH

3 2 3

2

3-(4-methylcyclohexyl)propane-1,2-diol

1

When a complex sidechain contains a chain that is attached to the parent hydrocarbon at a position other than at the end of the chain, the carbon of attachment is still numbered as C1 and the other part of the chain is named as a substituent group to that chain. 1 3

1

2

2

3

4

4

(1-ethylbutyl)benzene 1-(2-ethyl-1-methylbutyl)-2-methylcyclohexane Note: An alternate method of numbering the sidechain is to find the longest chain and begin numbering at the end closest to its attachment to the parent hydrocarbon. The –yl ending is added to the chain parent name and the position of the attachment is placed before the –yl ending. 1 2

3

4

5

1-(3-ethylpentan-2-yl)-2-methylcyclohexane

The table below shows some examples of IUPAC names for commonly known compounds. The IUPAC system allows the trivial names of these compounds to be retained as official IUPAC names and, for some, to be used in naming substituted compounds such as 4-bromobenzoic acid. The IUPAC systematic name for this compound would be 4-bromobenzenecarboxylic acid. OH

IUPAC: Trivial (retained)

N

azabenzene pyridine

1,2-dehydrobenzene benzyne

NH2

benzenol phenol

NH2

NH2

CH3

IUPAC: Trivial (retained)

phenylazane benzenamine aniline O

2-methylphenylazane 2-methylbenzenamine ortho-toluidine

naphthalene-2-ylazane naphthalene-2-amine 2-naphthylamine

O

O

OH

OCH3

IUPAC: Trivial (retained) benzenecarboxylic acid benzoic acid

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CH3

O

CH CH2

C

IUPAC: Trivial (retained)

H3C

methylbenzene toluene

CH3

propan-2-one

(ethenyl)benzene styrene

acetone Many other trivial names are also retained but can only be used for the unsubstituted compound. For example, the names butanoic acid (systematic) and butyric acid (trivial retained) are both approved by the 4-bromobutanoic acid and IUPAC. However, BrCH2CH2CH2COOH must be named systematically as cannot be named as 4-bromobutyric acid.

Hantzsch-Widman System Element Valence Prefix Element Valence Silicon IV Sila Oxygen II Sulfur II Thia Tin IV Selenium II Selena Tellurium II Boron III Bora Nitrogen III Stems for the Hantzsch-Widman System The stem for six-membered rings depends on the least heteroatom whose name directIy precedes the stem.

Prefix Oxa Stanna Tellura Aza Phosphorus III

Phospha

preferred heteroatom in the ring i.e., the

To determine the proper stem for six-membered rings, select the set below that contains the least preferred heteroatom before consulting the table. Ring size 3 4 5

Unsaturated irene ete ole

Saturated irane etane olane

Ring size 7 8 9

Unsaturated epine ocine onine

Saturated epane ocane onane

Common nomenclature Common nomenclature is an older system of naming organic compounds. Instead of using the prefixes for the carbon skeleton above, another system is used. The pattern can be seen below. Number of carbons

Prefix as in new system

Common name for alkanol

Common name for aldehyde

Common name for acid

1

Meth

-

Formaldehyde

Formic acid

2

Eth

-

Acetaldehyde

Acetic acid

3

Prop

-

Propionaldehyde

Propionic acid

4

But

-

Butyraldehyde

Butyric acid

5

Pent

Amyl alcohol

Valeraldehyde

Valeric acid

6

Hex

-

Caproaldehyde

Caproic acid

7

Hept

Enanthyl alcohol

Enanthaldehyde

Enanthoic acid

8

Oct

Capryl alcohol

Caprylaldehyde

Caprylic acid

9

Non

-

Pelargonaldehyde

Pelargonic acid

10

Dec

Capric alcohol

Capraldehyde

Capric acid

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A. Common Parent Ring Systems 8

1

8

7

2

7

3

6

9

1 2

or 6 5

benzene

4

3 5

naphthalene

10

4

anthracene

B. Monosubstituted Benzenes 1. Most substituents keep their designation, followed by the word “benzene”: Cl NO2 CH2CH3

chlorobenzene

nitrobenzene

ethylbenzene

COOH

benzoic acid

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2. Some common substituents change the root name of the ring. IUPAC accepts these as root names, listed here in decreasing priority: SO3H

CHO

benzenebenzaldehyde sulfonic acid

OH

NH2

phenol

aniline

OCH3

anisole

CH3

toluene

C. Disubstituted Benzenes 1. Designation of substitution—only three possibilities: X X

X

Y

Y common: IUPAC:

ortho1,2-

Y para1,4-

meta1,3-

2. Naming disubstituted benzenes—Priorities determine root name and substituents Br COOH HO NH2

OCH3

Br CHO 3-aminobenzoic acid 1,4-dibromobenzene 2-methoxybenzaldehyde

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D. Polysubstituted Benzenes CH3 Cl HN CH3

O2N

COOCH2CH3 NO2

Cl

OH NO2

3,4-dichloro-N-methylaniline

NH2

2,4,6-trinitrotoluene ethyl 4-amino-3-hydroxybenzoate (TNT)

E. Aromatic Ketones A special group of aromatic compounds are ketones where the carbonyl is attached to at least one benzene ring. Such compounds are named as “phenones”, the prefix depending on the size and nature of the group on the other side of the carbonyl. These are the common examples: O O C CH3 C CH2CH3 propiophenone

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acetophenone

O C CH2CH2CH3

butyrophenone

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O C

benzophenone

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Characteristics of organic compounds

•

Homologous series Compounds with the same functional group, differing only in the number of CH2 units in their skeleton are said to be in the same homologous series. They are part of the same family of compounds with similar reactions and characteristics that differ only in the number of carbon atoms that make up the chain. Members of a series will have formula that are linked by a general formula. For example, all alkanes have the general formula CnH2n+2. All organic compounds have six identifying characteristics each. 1. Molecular formula - showing the actual number of atoms of each element in that compound. E.g. C2H4O2 for ethanoic acid, meaning there are two carbon atoms, four hydrogen atoms and two oxygen atoms. 2. Empirical formula - the simplest whole number ratio of the atoms of each element in that compound. E.g. CH2O for ethanoic acid, meaning there is a ratio of 1:2:1 of C:H:O atoms.

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3. Structural formula - showing how those atoms are arranged. E.g. CH3CO2H for ethanoic acid, meaning three hydrogen atoms are attached to one carbon atom, which in turn is attached to another carbon atom, which in turn has two oxygen atoms attached to it, one of which has a hydrogen atom attached to it. 4. Graphical formula - showing how these atoms are arranged in space and the bonds between them. Lines represent covalent bonds (shared pairs of electrons) between atoms. E.g. for ethanoic acid, where = represents a double covalent bond and – represents a single covalent bond.

H H

C H

O C O

H

5. Skeletal formula – showing an abbreviated form of the carbon chain, with each line segment understood to have a carbon atom at each end. These structures may or may not show terminal (end of chain) carbons. E.g. for ethanoic acid

O

O OH Or

H3C

OH

6. Name - based upon an accepted system for naming compounds (IUPAC nomenclature). E.g. CH3CO2H, is called ethanoic acid.

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ALKANES 1. Name the following compounds i) CH3C(CH3)2CH2CH3

ii) CH3CH2C(C2H5)2CH2CH2CH3 iii) CH3CH(CH3)CH2CH(CH3)CH3 iv) CH3CH2CH(CH3)CH(C2H5)CH2C(CH3)2CH3 2. Draw graphical formula for the following compounds 2-methylpropane 3-methylheptane 2,3-dimethylbutane 2,2,6-trimethyloctane 1,3-diethylcyclobutane

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i) ii) iii) iv) v)

ALKENES & ALKYNES 3. Name the following compounds i) ii) iii) iv) v)

CH3CH2CH=CH2 CH3C≡CCH3 CH3CH2CH(CH3)C≡CCH3 CH3C≡CCH(CH3)2 CH2=CHCH=CH2

4. Draw graphical formula for the following compounds i) ii) iii) iv) v)

2,3-dimethylbut-2-ene 4-methylhex-1-yne 3,4-diethylhex-2-ene 4-ethylcyclohex-1-ene 4-ethylcyclohex-1-ene

HALOGEN COMPOUNDS 5. Name the following compounds i) CH3CH2CH2CH2CH2I

Br O

ii) iii)

(CH3)2CHBr

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6. Draw graphical formula for the following compounds i) 2-iodo-2-methylpentane ii) 1-chloro-1-bromoethane iii) triiodomethane iv) 1-bromo-3-chloro-4-methylhexane ALCOHOLS 7. Name the following compounds i) CH3CH2CH(OH)CH2CH3 ii) CH3C(CH3)(OH)CH2CH3 iii) CH3CH(OH)CHBrCH3 8. Draw graphical formula for the following compounds i) pentan-2-ol ii) 3-methylhexan-1-ol iii) cyclohexane-1,3-diol ALDEHYDES & KETONES 9. Name the following compounds

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i) CH3CH2CH2CHO ii) CH3CH(CH3)COCH3 iii) CH3CH(CH3)CHO iv) CH3CH(CH3)COCH3 10. Draw graphical formula for the following compounds i) cyclohexanone ii) 3-methylbutanal iii) 2,2-dimethylpropanal iv) 3-chlorobutan-2-one CARBOXYLIC ACIDS & DERIVATIVES 11. Name the following compounds i) CH3CH2CO2H ii) CH3CH2CH(OH)CH2COOH iii) (CH3)3CCO2H Cl H3C

iv) H3C

O

12. Draw graphical formula for the following compounds i) pentanoic acid ii) 3-aminopropanoic acid iii) butenedioic acid iv) chloroethanoic acid v) methylpropanoate NITROGEN COMPOUNDS 13. Name the following compounds i) CH3CH2CN ii) (C2H5)3N 14. Draw graphical formula for the following compounds i) 2-methylbutanonitrile ii)

3-aminopentane

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Name the following compounds according to IUPAC rules:

1

2

3

Br

4

5

6

8

9

Cl

7

Br Cl

10

11

12 Br

Cl

Answer Key: Alkane Nomenclature 1. 2,3-dimethyl-5-propylnonane 2. 4-bromo-2,2,7,8-tetramethylnonane 3. 3-ethyl-2,4,6,7-tetramethylnonane 4. 2,3-dimethyl-6-[1,2-dimethylpropyl]decane 5. 2,7-dimethyl-5-[1,1-dimethylpropyl]nonane 6. 1-isopropyl-4-methyl-2-propylcyclohexane 7. 1-chloro-1-cyclopentyl-4,4-dimethylheptane 8. 7-bromo—3-cyclopropyl-6-ethyl-2,6-dimethylnonane 9. 3-chloro-1,1-dimethylcyclopentane 10. cis-1-isopropyl-3-methylcyclohexane 11. 2-bromo-4-sec-butyl-1,7-dimethylcyclodecane 12. 1-chloro-2-isopropyl-1,5-dimethylcyclooctane

Aldehydes and Ketones: Nomenclature Problems: Name the following according to IUPAC rules. O

1.

O

2.

H

H

O

3.

4.

O OH

5.

O

6.

O

HO

H O

O O 7.

8.

OH

O H

O 9.

10. O O O

11.

12. O

OH 13.

14. O

Br

O O

H

Aldehydes and Ketones: Nomenclature Answers 1. 4-ethyl-5-methyloctanal 2. 3-n-butyloctanal (or 3-butyloctanal) 3. 6-isopropyl-7-decen-5-one 4. 6-hydroxy-5-methyl-2-hexanone 5. 2,7-octanedione 6. 9-hydroxy-6-oxononanal 7. 3-pentylcyclohexanone 8. 7-hydroxy-3-octenal 9. 4-[2,2-dimethylpropyl]cyclohexanone 10. 1,3-cyclohexanedione 11. 3-[3-hydroxypentyl]cyclohexanone 12. 1-cyclopentyl-2-hexanone 13. 2-[3-oxobutyl]cyclopentanone 14. 2-[1-bromopropyl]hexanal

. : 1.1

Give the IUPAC name of each of the compounds shown. a) CH3 CH2 CH2 CH2 CH3

c) CH3 CH2 CHCH 3 | OH

d) CH3 CH2 CHCH 2 CH3 | CH3

e) (CH3 )2 CHCHBrCH 2 CH3

f) (C2 H5 )2 CH(CH 2 )2 CH3

g)

h) CH3 CBr2 CH2 CCl3

i) CH3 CH2 CHCH 2 CH2 CH3 | CH2 OH

j) (CH3 )2 CHCH 2 CH2 C=CH 2 | CH3

k)

l) CH3 CH2 C Br 1.2

b) CHCl3

Br C

CH3 CH3 | | CH3 CH2 CHCH 2 CHCHCH 3 | CH2 CH2 CH3

CH3 | CH3 CH2 C-C≡C-CH(CH 3 )2 | CH3

m) CH3 CH2 C

H

CH3 CH2

H C H

Draw the structure of each of the compounds named below. a) 2,2-dimethylbutane

b) 3,3-dimethyl-1-butanol

c) 4-ethyl-2,2-dimethylhexane

d) 1,2-dibromo-2-methylpropane

e) 4-methyl-2-pentyne

f) cis-1-bromo-2-pentene

2.1

2.2

3.1

Give the IUPAC name of each of the compounds shown. CH3 a) b) (CH3 )2 CH c) OH

d) Cl

Draw the structure of each of the compounds named. a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol

Cl

c) 4-isopropylcyclohexene

Give the name of each of the compounds shown. CH3 a)

b)

c) Cl

d) CH3

3.2

Draw the structure of each of these compounds. a) bicyclo[2.2.0]hexane b) 2-isopropylbicyclo[1.1.0]butane c) 1,5-diethylbicyclo[3.3.0]octane

4.1

Give the common name of each of the compounds shown. a) CH3 CH2 OH b) CH3 CH2 CH2 Cl c) (CH3 )3 C-CH2 OH

d) FC(CH3 )3

Draw the structure of each of the compounds named. a) methyl iodide b) isobutyl alcohol c) isopropyl alcohol

d) sec-butyl bromide

4.2

5.1

Give the common name of each of the following compounds. Br OH a) b) c) OH

5.2

Draw the structures of the following compounds. a) cyclopropyl chloride b) cyclohexyl iodide

6.

Draw the structures of each of the following compounds. a) propylene b) acetylene c) ethylacetylene

d) ethylene

SOLUTIONS TO SAMPLE PROBLEMS: 1.1

a) pentane b) trichloromethane c) 2-butanol d) 3-methylpentane e) 3-bromo-2-methylpentane f) 3-ethylhexane g) 5-isopropyl-3-methyloctane h) 3,3-dibromo-1,1,1-trichlorobutane i) 2-ethyl-1-pentanol j) 2,5-dimethyl-1-hexene k) 2,5,5-trimethyl-3-heptyne l) trans-1,2-dibromo-1-butene m) 2-ethyl-1-butene

1.2

a) 2,2-dimethylbutane CH3 | CH3 CCH2 CH3 | CH3

b) 3,3-dimethyl-1-butanol CH3 | HOCH 2 CH2 CCH3 | CH3

c) 4-ethyl-2,2-dimethylhexane d) 1,2-dibromo-2-methylpropane CH3 CH2 CH3 CH3 | | | CH3 CCH2 CHCH 2 CH3 CH2 CCH3 | | | CH3 Br Br e) 4-methyl-2-pentyne CH3 C≡CCHCH 3 | CH3

f) cis-1-bromo-2-pentene BrCH2 CH2 CH3 C

C H

H 2.1

a) cycloheptane c) 2-methylcyclobutanol

2.2

a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol c) 4-isopropylcyclohexene CH3 | CH3 CH3 HO CH2 C-CH3 | CH3 a) bicyclo[4.3.0]nonane b) bicyclo[3.2.1]octane c) 7-chlorobicyclo[4.1.1]octane d) 1,6-dimethylbicyclo[3.2.0]heptane

3.1 3.2

b) isopropylcyclopentane d) 1,4-dichlorocyclohexene

The structures are: CH2 CH3 a)

b)

CH(CH 3 )2

c) CH2 CH3

4.1

a) ethyl alcohol b) propyl chloride c) neopentyl alcohol d) tert-butyl fluoride

4.2

a) methyl iodide

b) isobutyl alcohol

CH3 I

(CH3 )2 CHCH 2 OH

5.1

a) cyclopentyl alcohol

5.2

a) cyclopropyl chloride

a) propylene CH3 CH=CH 2

(CH3 )2 CHOH

b) cyclohexyl alcohol

d) sec-butyl bromide CH3 CHBrCH 2 CH3

c) cyclobutyl bromide

b) cyclohexyl iodide

Cl

6.

c) isopropyl alcohol

I

b) acetylene H-C≡C-H

c) ethylacetylene CH3 CH2 C≡C-H

23

d) ethylene H2 C=CH 2